Hydrochloric Acid → 3-(5-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)isoindolin-2-yl)propanoic acid

To a solution of methyl 3-(5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)isoindolin-2-yl)propanoate (21 mg, 0.048 mmol) in ethanol (1 ml) was added 2M aqueous NaOH (1 ml, 2.000 mmol). The reaction was stirred at room temperature under an atmosphere of nitrogen for approximately 4 hours. Reaction mixture was then acidified to a pH of I by addition of 2N HCl, at which time a precipitate formed. The solid was collected by filtration and washed with water (3×5 mL). The solid was then dried in a vacuum oven overnight to give 3-(5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)isoindolin-2-yl)propanoic acid as the hydrochloride salt (10.2 mg, 46.2%). LCMS (Table 1, Method c) Rt=1.86 min, m/z 428.20 (M+H)+. 1H NMR (400 MHz, DMSO) δ ppm 12.12 (m, 1H), 8.23 (s, 1H), 8.19 (d, 1H), 8.07 (d, 1H), 8.01 (dd, 1H), 7.68 (d, 1H), 7.41 (d, 1H), 4.83 (sept, 1H), 4.72 (s, 4H), 3.58 (t, 2H), 2.84 (t, 2H), 1.36 (d, 6H)